Triethylamine → 1-Ethyl-5-(ethylthio)carbonyloxypyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone

HRID 1661952Notes

Reaction equation

HRID 1661952 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:25])=[C:7]([C:15]([C:17]2[CH:18]=[N:19][N:20]([CH2:23][CH3:24])[C:21]=2[OH:22])=[O:16])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[O:4].C(N(CC)CC)C.[CH3:33][CH2:34][S:35][C:36](Cl)=[O:37]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:25])=[C:7]([C:15]([C:17]2[CH:18]=[N:19][N:20]([CH2:23][CH3:24])[C:21]=2[O:22][C:36]([S:35][CH2:34][CH3:33])=[O:37])=[O:16])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18056Ethyl chlorothioformateHCID 178463120HCID 178463120, compound

Product 1

HCID 872334581-Ethyl-5-(ethylthio)carbonyloxypyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketoneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Hydroxy-1-ethylpyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (510 mg, 1.39 mmol) was dissolved in dry tetrahydrofuran-(20 mL), and triethylamine (281 mg, 2.78 mmol) was added thereto. A solution (4 mL) of 96% S-ethyl chlorothiolformate (217 mg) dissolved in dry tetrahydrofuran was added thereto little by little under cooling with ice water. The reaction mixture was stirred for 90 minutes while the reaction temperature was allowed to warm to room temperature. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product as an oil (417 mg, 0.92 mmol) (yield: 66%)

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-f6c6655684dd4492b154205d251fe842
Source dataset
uspto-grants-2011_10
Patent number
US08030498B2

Reaction notes

Loading…